This invention relates to novel alkenylsulfonylureas and their use as pre- or post-emergence herbicides and plant growth regulants.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. PA1 R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA1 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA1 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom; PA1 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA1 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA1 W and Q are independently oxygen or sulfur; PA1 n is 0, 1 or 2; PA1 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA1 Y is methyl or methoxy; or their agriculturally suitable salts; provided that: PA1 R.sub.1 is H, F, Cl, Br or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.2 is H, F, Cl, Br or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.3 is H or CH.sub.3 ; PA1 R.sub.4 is C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.dbd.CH.sub.2 ; PA1 R.sub.5 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.6 is C.sub.1 -C.sub.3 alkyl; or PA1 R.sub.5 and R.sub.6 may be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; PA1 R.sub.7 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.8 is C.sub.1 -C.sub.4 alkyl; PA1 m is 0, 1 or 2; PA1 A is ##STR11## X is Cl, CH.sub.3 or OCH.sub.3 ; Y is CH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH(OCH.sub.3).sub.2 or ##STR12## Z is CH or N; X.sub.1 is H, Cl, CH.sub.3, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; and PA1 Y.sub.1 is CH.sub.3 or OCH.sub.3 ; PA1 (1) when R is halogen and R.sub.1 and/or R.sub.2 are halogen, then the values of R, R.sub.1 and R.sub.2 must be the same; PA1 (2) when R.sub.1 and R.sub.2 are halogen, then the values of R.sub.1 and R.sub.2 must be the same; PA1 (3) the total number of carbon atoms of R.sub.5 and R.sub.6 is less than or equal to 5; PA1 (4) when X is Cl, then Z is CH and Y is OCH.sub.3, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 (5) R.sub.1 and R.sub.2 are not simultaneously H; and PA1 (6) when L is ##STR13## PA1 (1) Compounds of Formula I where L is ##STR14## (2) Compounds of Formula I where L is ##STR15## (3) Compounds of preferred 1 where: R is Cl, Br, C.sub.1 -C.sub.3 alkyl, CO.sub.2 R.sub.4 or SO.sub.2 R.sub.7 ; PA1 (4) Compounds of preferred 3 where R is CO.sub.2 R.sub.4. PA1 (5) Compounds of preferred 2 where L is ##STR16## (6) Compounds of preferred 5 where R is CO.sub.2 R.sub.4 ; PA1 (7) Compounds of preferred 6 where A is ##STR17## (8) Compounds of preferred 2 where L is ##STR18## (9) Compounds of preferred 8 where R is CO.sub.2 R.sub.4 ; PA1 (10) Compounds of preferred 9 where A is ##STR19## PA1 X=CH.sub.3 or OCH.sub.3. PA1 X=CH.sub.3 or OCH.sub.3. PA1 Z is as previously defined.
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein R.sub.1 is hydrogen or lower saturated aliphatic acyl; and
The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR3## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR4## wherein R is butyl, phenyl or ##STR5## and R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6##
U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula: ##STR7## wherein R.sub.1 is ##STR8## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA2 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA2 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA2 R.sub.4 is C.sub.1 -C.sub.3 alkyl; and PA2 R.sub.3 is H. PA2 R.sub.4 is C.sub.1 -C.sub.3 alkyl; and PA2 R.sub.3 is H. PA2 R.sub.4 is C.sub.1 -C.sub.3 alkyl; and PA2 R.sub.3 is H.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, barley, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.